The Treachery of Optimism

I used to own a business. It was successful, and I’m very proud of it – but it wasn’t a home run. Most of the time it was just successful enough to not be a failure. I paid enough of my bills every month to avoid serious discomfort. When things were good, we caught up. When life was expensive, we fell behind.

The service I offered – a backup and security product for WordPress websites called CodeGarage – came with stress. The code didn’t always work right, and when it went bad, people were occasionally left hanging. If customers got hacked, or new customers needed help cleaning up the mess left by hackers, they were impatient to see results and have things get back to normal. I worked a lot of late nights, cleaning up problems and helping customers. I enjoyed the work, but the stresses it created were not trivial.

Over time I grew tired of the endless financial stress, and felt like I was stagnating professionally. I wasn’t growing as a developer or a business owner, I was just keeping my head above water. In an effort to figure out how to keep moving forward, I applied to, and eventually sold CodeGarage to Automattic (the company behind WordPress.com), joining them as a developer. Personally and professionally, this was a huge victory; vindication that the hard work of the prior years was worthwhile. To top it off, Automattic was (and continues to be) a dream job — a company I had watched and admired for years, which turned out to be even better on the inside than it appeared on the outside.

Overnight, my lifestyle changed significantly. I had gone from a struggling small business owner to an employee. I knew exactly how much money I’d make every month. It was enough money, every time. I knew when it would hit my bank account. I even had health insurance. Real health insurance.

Not all the change was financial. I slept more, and I slept better. I was easier to be around. I could take time off. I lost weight. I could go an entire weekend without working. The release of stress and the accompanying benefits was not slow and gradual – it was abrupt, and obvious.

But somehow, things felt off. I was restless. Uncomfortable. In spite of the fact that I was making enough money to live comfortably, my work/life balance was better, and my stress was way down, I couldn’t shake the idea that something was missing.


My entire adult life had been about hustle: after eeking out a high school diploma, I floundered at community college. Soon after, I found myself working in a factory. I was unhappy, and I knew I could do better. So, in those long nights on the factory floor, I convinced myself that things could get better. Hard work could create a better career, a better life.

Struggle became my life, my mantra. Each step along the way was a victory – the first time I convinced someone to let me build a website for them. The first time I won a job on rentacoder.com. The first paying customers for my SAAS business. The most crucial piece though — the thing that made it all tolerable, even exciting — was the dream. Owning a big, self-sustaining business. Thousands of customers. Financial freedom. The big payout.

Struggling to get by, and to convince myself (and those around me) that owning a business is a good idea, I felt like I had to dream big. Working long hours and dealing with constant stress (financial and otherwise) didn’t feel worth it if the payout was just an unstable income, and less flexibility than a normal employee has.

As a business owner, it’s easy to believe that you’re just one big deal, one solid marketing campaign, one killer feature away from massive growth. This optimism isn’t necessarily irrational. CodeGarage saw at least 2 occasions that worked exactly like this: events, ideas, or sales that singularly propelled the business to a new level. Without the continuous belief that things will continue working out, and continue growing, I’d have quit or failed long before any money was made. This was the required mindset in order to keep going. However: it came with side effects.

Since I was convinced that I was just a few good decisions, ideas, or turns of fate away from greater success, I knew that these things would come to me. They’d happen, and probably soon. Success was not a question of if, but when, and more than that, it was “how soon”.

In practice, that meant I knew that within some period of time, the business would be successful enough that any of my current problems — work/life balance, money, stress — would disappear. So why bother worrying about them?

Assuming that impending success will solve all of your problems is a bit like praying instead of going to the doctor. It gave me the acute ability to ignore, or at least postpone dealing with problems. Financial problems (say, the massive expense of childbirth without maternity coverage, or poorly calculated tax liabilities) in particular were easy to ignore, as I was convinced greater success would soon solve them.

Of course, living like this is precarious. I slowly realized that while it did just take a few events to massively change a business, I might not have the requisite skills to facilitate those events, or I might not be able to learn them as quickly as circumstance demanded. Most terrifying, they might come too late. I was fortunate to land at Automattic, where I can continue to learn and grow. Maybe someday I’ll end up running a business again – this time with a new array of skills and tools to find success.

This brings me back to the vaguely unsettled feeling I developed after a time in my new, stable job. I had grown to believe massive (and most importantly, financial) success was just around the corner, all the time. In many ways, moving to my current job is that success I sought. However, it’s not “buy a yacht” success. Or “Own a second home at a ski resort” success. It is “Improve your skills working on interesting projects with smart people while not having to worry about whether your child can go to the doctor next month” success.

Having a job with a stable income, and compensation not tied directly to performance (at least, not in the way it is as a business owner) has meant accepting that I’m not going to buy a yacht next year. Conversely, it meant that I could buy a comfortable house this year. Much more importantly, it means that any financial problems I run into actually have to be dealt with, and not put off until the next theoretical deal can erase them. It’s a bit like losing touch with an old, fun loving, terribly irresponsible friend.

I’ll miss you, buddy.

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